I went through this exact same situation two years ago with H&R Block software having similar issues with Form 5329. Here's what I learned from my experience: You absolutely CAN file Form 5329 separately - it's completely legitimate and the IRS processes these all the time. Go ahead and file your 1040 now to get your refund, then handle the 5329 separately. A few key tips that saved me headaches: 1. Use the actual PDF form from irs.gov instead of trying to fix the software 2. For the medical hardship waiver, you'll check box "01" in Part I and write a brief explanation 3. Mail it to the same processing center where you filed your 1040 (check the IRS website for your state's address) 4. Keep copies of EVERYTHING for your records The medical hardship exception is pretty straightforward if your medical expenses exceeded 7.5% of your AGI (it was 10% in previous years but they lowered it). Just document that the early withdrawal was necessary to pay those qualifying medical expenses. Don't stress about the April deadline for this - Form 5329 filed separately doesn't have the same strict deadline as your main return, though you'll want to get it done soon to avoid any penalty interest accumulating.

I want to add some reassurance here - you're definitely not alone in having software issues with Form 5329! I've seen this same problem reported across multiple tax software platforms this year, especially with the hardship waiver sections. Since you mentioned you're worried about the April deadline, here's what I'd recommend: Go ahead and file your 1040 now to secure your refund and meet the main deadline. You can absolutely file Form 5329 separately afterward - it's a completely legitimate approach that many taxpayers use when software glitches occur. For the medical hardship waiver, you'll want to prepare a clear written statement explaining your situation. Include specific details about your medical expenses, dates, and how the early withdrawal was necessary to cover these costs. Make sure your medical expenses exceeded 7.5% of your adjusted gross income to qualify for the exception. The key is having good documentation - medical bills, receipts, doctor's notes, etc. Attach these to your Form 5329 along with your written explanation. The IRS reviewers handle these cases regularly, so a straightforward, well-documented submission usually processes without issues. Don't let the software bug derail your entire tax filing process. File your main return now, then tackle the 5329 separately with the proper documentation. You've got this!

This is really encouraging to hear! I filed on February 7th and have been in the same waiting pattern - blank transcript for weeks despite checking multiple times daily. As another 1099 contractor, I was starting to worry that something was wrong with my filing since I keep seeing posts about people getting their refunds already. Your 6-week timeline from filing to transcript update actually seems pretty consistent with what I'm seeing from other contractors in this thread. Did you have any business deductions or expenses that might have added to the processing time? I'm trying to figure out if certain elements of contractor returns typically take longer to review.

Thanks for sharing this update! I filed on February 3rd and my transcript just updated yesterday with the same cycle 0905. It's been such a relief to finally see some movement after weeks of that blank page. I'm also a 1099 contractor and was starting to worry that something was flagged with my return. Your timeline of about 6 weeks matches mine almost exactly. For anyone still waiting - I noticed my transcript updated overnight on a Tuesday, so it might be worth checking early in the morning if you haven't been doing that already. The cycle code explanation from earlier in this thread was really helpful too - I had no idea what those numbers actually meant!

I went through this exact same situation last year with my dog walking side business! The good news is TurboTax makes it pretty straightforward once you know the steps. When you get to the business income section, you'll enter your 1099-K information using your SSN as the tax ID. TurboTax will automatically generate Schedule C for your self-employment income. The key thing is to make sure you enter the gross amount from Box 1a of your 1099-K - that's what Square reported to the IRS. One thing that really helped me was keeping a simple spreadsheet throughout the year tracking all my business expenses. Beyond the Square processing fees, don't forget about: - Hair styling tools and equipment - Products you use on clients - Any licensing or certification costs - Transportation to client locations - Even a portion of your home wifi if you use it to manage bookings Also be prepared for the self-employment tax hit - that caught me off guard my first year. You'll owe both regular income tax plus the additional 15.3% for Social Security and Medicare on your net profit. Setting aside about 25-30% of your side business income throughout the year helps avoid a big surprise at tax time. The most important thing is just being honest and thorough with your reporting. The IRS isn't trying to trick you - they just want to make sure the income matches what was reported by Square.

Just wanted to add something important that hasn't been mentioned yet - make sure you're keeping detailed records of ALL your cash transactions too, not just what shows up on the 1099-K! The 1099-K from Square only reports your electronic payments, but if you're doing haircuts and styling, you probably also receive cash tips or some clients might pay cash directly. The IRS expects you to report ALL your income, not just what's on the 1099-K form. I learned this the hard way when I got audited for my massage therapy side business. Even though my 1099-K showed most of my income, the auditor asked for records of any cash payments too. Now I keep a simple log of every service I provide, whether paid by card through Square or cash. Also, since you mentioned you didn't set up the tax settings correctly in Square, you'll want to be extra careful about sales tax if your state requires it for personal services. Some states exempt personal services like haircuts from sales tax, but others don't. You might need to file separate sales tax returns depending on your location. TurboTax won't help with state sales tax obligations - that's usually handled through your state's department of revenue. Worth looking into before you file your income taxes!

I went through this exact situation two years ago with a state contractor role. Here's my experience and some additional tips: First, definitely file your taxes now using Form 8919 with code G as others have mentioned. The SS-8 process is painfully slow - mine took 11 months to get resolved, but it was worth it in the end. One thing I didn't see mentioned is that you should also consider filing Form 8888 if your partner had any taxes withheld from her paychecks. If they were treating her like an employee in practice (withholding taxes) but classifying her as a contractor on paper, that's even stronger evidence of misclassification. Also, document EVERYTHING about the work relationship: did they provide training? Set her schedule? Require her to work on-site? Control how she did the work? These are the key factors the IRS looks at. I created a detailed timeline of all my interactions with the employer showing they controlled every aspect of my work. The missing 1099 is definitely concerning - contact them immediately since you need those numbers to file. If they refuse to provide it or claim they "don't have to" because she was a contractor, that's actually more evidence in your favor that something's fishy with their classification. Stay persistent with the process. It's frustrating but worker misclassification is a real problem, especially with government contracts trying to save money on benefits and taxes.

Based on everything discussed here, it sounds like you have a really strong case for misclassification. The fact that they controlled her schedule, provided training, required approval for time off, and had her use their timesheet system are all classic indicators of an employee relationship. One additional tip I'd add: when you submit your SS-8, include a cover letter that clearly summarizes the key facts and references specific IRS guidelines. I've seen cases move faster when the reviewer can quickly understand the situation without having to dig through all the documentation. Also, don't be discouraged by the long timeline others have mentioned. While the SS-8 process is slow, using Form 8919 with code G gives you the tax benefits immediately. You're essentially getting the best of both worlds - immediate tax relief and official determination for future reference. Make sure to send your SS-8 via certified mail so you have proof of when the IRS received it. This can be important for timing purposes and shows you're taking the process seriously. Good luck with everything - it sounds like you're handling this exactly the right way!

I went through this exact same situation with my daughter when she turned 18 and started college! You're absolutely right that you can claim her as your dependent while she files her own return - this is actually a really common arrangement for college students with part-time jobs. Based on what you've described, you clearly meet all the requirements for claiming her as a qualifying child: she's under 24, a full-time student, lives with you more than half the year (college counts as temporary absence), and most importantly - you're providing way more than half her support. When you're covering tuition, housing, food, medical insurance, phone, and other major expenses while she only makes $800-900/month, the math is pretty straightforward. Here's how it works: Your daughter files her own return for her mall job income and makes sure to check the box that says "Someone can claim you as a dependent." She'll still get back most of what was withheld from her paychecks as a refund. You claim her as your dependent on your return and can take advantage of education tax credits like the American Opportunity Credit, which can save you up to $2,500. One important tip - have your daughter review her W-4 at work to make sure her withholding is set up correctly as a dependent. This helps avoid any surprise tax bills at the end of the year. Most employers are very familiar with helping student employees get this right. It really is a win-win situation when done properly - you both benefit financially and everything stays above board with the IRS!

This is such a helpful thread! I'm in a very similar situation with my 18-year-old who just started college and has a part-time job at a local bookstore. Reading through everyone's experiences has really clarified things for me. One thing I wanted to add that I learned from our tax preparer - if your daughter has any 1098-T forms from her college showing tuition payments, make sure to keep those organized. Since you're claiming her as a dependent and paying for her education expenses, you'll need those forms to claim the American Opportunity Credit. Also, I discovered that even though my daughter's scholarship covers part of her tuition, I can still claim the education credit for the portion I pay out of pocket. The scholarship money doesn't count against the support test either, which was a relief since I was worried it might complicate things. Thanks to everyone who shared their experiences - it's so reassuring to know this is a common situation that many families navigate successfully!